1-(thiophen-2-yl)hexane-1,5-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(thiophen-2-yl)hexane-1,5-dione
• 英文别名: 1-(2-thienyl)-1,5-hexanedione；2-(5-oxohexanoyl)thiophene；1-Thiophen-2-ylhexane-1,5-dione
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: SITKUWPKAHXCKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基噻吩 在 四氯化锡 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-(thiophen-2-yl)hexane-1,5-dione
  参考文献：
  名称：

  Sasaki, Tadashi; Ishibashi, Yukio; Ohno, Masatomi, Journal of Chemical Research, Miniprint, 1984, # 7, p. 1972 - 1997

  摘要：

  DOI：

文献信息

• 1,5-Diketones from 3,4-dihydropyranones: An application in the synthesis of (±)-α-herbertenol
  作者：David C. Harrowven、Joanne C. Hannam

  DOI：10.1016/s0040-4020(99)00495-0

  日期：1999.7

  An approach to 1,5-diketones involving the addition of organolithium reagents to 3,4-dihydropyranones is described. Good yields are obtained when reactions are quenched with trimethylsilyl chloride prior to hydrolytic work up and the organolithium reagent contains a Lewis basic group adjacent to the carbon to lithium bond. The method has been applied in a short synthesis of the fungicidal sesquiterpene

  描述了一种涉及将有机锂试剂添加到3，4-二氢吡喃酮中的1，5-二酮的方法。当在水解后处理之前用三甲基甲硅烷基氯淬灭反应，并且有机锂试剂包含与碳至锂键相邻的路易斯碱性基团时，可获得良好的产率。该方法已用于杀真菌倍半萜烯（±）-α-香叶烯醇的短合成中。
• Ring-opening of tertiary cyclopropanols derived from β-diketones
  作者：Le-Zhen Li、Bin Xiao、Qing-Xiang Guo、Song Xue

  DOI：10.1016/j.tet.2006.05.064

  日期：2006.8

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.